J IRAN CHEM SOC
8 Hz), 2.49 (2 H, d, J: 8 Hz), 2.41 (2 H, d, J: 12 Hz), 2.35
(2 H, d, J: 12 Hz), 2.32 (2 H, d, J: 12 Hz), 2.31 (2 H, d, J:
12 Hz), 2.27 (2 H, d, J: 12 Hz), 2.26 (2 H, d, J: 12 Hz),
2.24 (2 H, d, J: 12 Hz), 2.18 (2 H, d, J: 12 Hz), 2.16 (2 H,
d, J: 12 Hz). 13C NMR (DMSO-d6, 400 MHz,): δ: 193.12,
191.59, 176.38, 164.53, 145.95, 144.16, 143.49, 141.69,
138.77, 134.19, 133.70, 132.47, 132.08, 130.96, 130.62,
130.22, 130.06, 129.95, 129.75, 129.59, 129.42, 129.26,
124.65, 122.81, 120.77, 119.24, 39.32, 21.75, 21.68, 21.41.
LC/MZ (70 eV, APC1): 1086.59 [M+ + H+].
(1 H, s), 9.84 (1 H, s), 9.71 (1 H, s), 9.16 (1 H, s), 8.88(1
H, s), 8.76 (2 H, t, J: 4 Hz), 8.73 (2 H, t, J: 12 Hz), 8.10 (2
H, t, J: 8 Hz), 8.08 (2 H, t, J: 8 Hz), 8.06 (4 H, t, J: 8 Hz),
8.02 (4 H, t, J: 16 Hz), 8.00 (4 H, t, J: 8 Hz), 7.91 (4 H, t,
J: 36 Hz), 7.89 (2H, t, J: 12 Hz), 7.86 (2 H, t, J: 12 Hz),
7.84 (2 H, t, J: 8 Hz), 7.82 (2 H, t, J: 8 Hz) 7.79 (1 H, d,
J: 16 Hz), 7.77 (4 H, d, J: 8 Hz), 7.73 (4 H, d, J: 24 Hz),
7.65 (4 H, d, J: 8 Hz), 7.63 (1 H, d, J: 8 Hz), 7.61 (2 H,
d, J: 8 Hz), 7.59 (1 H, d, J: 12 Hz), 7.57 (1 H, d, J: 8 Hz),
7.55 (1 H, d, J: 8 Hz), 7.53 (1 H, d, J: 12 Hz), 7.44 (1 H,
d, J: 4 Hz), 7.42 (1 H, d, J: 8 Hz), 7.40 (2 H, t, J: 4 Hz),
7.38 (2 H, t, J: 81 Hz), 7.36 (2 H, t, J: 8 Hz), 7.34 (2 H, t, J:
8 Hz), 2.53 (3 H, m), 2.49 (3 H, m), 2.36 (3 H, m), 2.32 (3
H, m). 13C NMR (DMSO-d6, 400 MHz,) δ: 191.80, 165.37,
147.94, 144.59, 141.23, 134.75, 132.34, 130.47, 130.24,
129.76, 129.59, 129.38, 129.15, 128.94, 128.35, 124.50,
123.72, 119.00, 116.04, 108.66, 107.73, 107.53, 39.93,
21.66, 21.39. LC/MZ(70 eV, APC1): 1038.10 [M+].
Bis [(1-((2-hydroxynaphthalen-1-yl)methyleneamino)-
2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)(p-tolyl)
methanone] platinum(II) chloride (4) was prepared using
[(1-amino-2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-
5-yl)(p-tolyl)methanone], 2-hydroxy-1- naphthaldehyde,
and platinum(II) chloride. It was obtained as a reddish-
brown solid, yield 44%; m.p. 291 °C (disintegration); UV
(EtOH) λmax (log ε) 344.6 (5.33) nm; FTIR γmax 750, 1280,
1
1602 cm−1; H NMR (DMSO-d6, 400 MHz,): δ: 10.00 (1
H, s), 10.01 (1 H, s), 8.90 (1 H, s), 8.80 (1 H, s), 8.70 (1 H,
s), 8.60 (1 H, s), 8.30–6.80 (28 H, m) 2.49 (2 H, d, J: 8 Hz),
2.41 (2 H, d, J: 12 Hz), 2.37 (H, s), 2.33 (H, s), 2.31 (H, s),
2.29 (H, s), 2.26 (H, s), 2.24 (H, s), 2.18 (H, s), 2.16 (H,
s). 13C NMR (DMSO-d6, 400 MHz,): δ: 193.21, 192.49,
175.28, 164.55, 146.95, 144.22, 143.54, 141.80, 139.22,
134.23, 133.81, 132.39, 132.05, 131.06, 130.80, 130.32,
130.04, 130.05, 129.88, 129.49, 129.40, 129.15, 124.45,
122.92, 121.07, 119.22, 39.32, 21.80, 21.88, 21.54.LC/
MZ(70 eV, APC1): 1175.25 [M+ + H+].
Biological activity evaluation
formed according to the literature [12].
Minimal inhibitory concentration
Minimal inhibitory concentrations (MIC) [13–17] were
determined by the microdilution broth method following
the procedures recommended by the National Committee
for Clinical Laboratory Standards (NCCLS, 2000). Tri-
methoprim and tetracycline were used as standard drugs.
Bis
[(1-((2-hydroxynaphthalen-1-yl)methyleneamino)-
2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)(p-tolyl)metha-
none] dichloro cupper(II) (5) was prepared using [(1-amino-
2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)(p-tolyl)
methanone], 2-hydroxy-1-naphthaldehyde, and cupper(II)
chloride. It was obtained as a light-brown solid, yield 48%;
m.p. 176 °C (disintegration); UV (EtOH) λmax (log ε) 475.8
(5.59) nm; FTIR γmax 1602, 1280, 759 cm−1. 1H NMR
(DMSOd6, 400 MHz,): δ: 11.86 (1 H, s), 11.81 (1 H, s), 9.92
(1 H, s), 9.86 (1 H, s), 9.76 (1 H, s), 9.59 (1 H, s), 9.56–6.60
(28 H, m), 2.85 (2 H, d, J: 8 Hz), 2.80–2.29 (10 H, m). 13C
NMR (DMSO-d6, 400 MHz,) δ: 191.58, 160.91, 145.93,
145.15, 141.73, 134.19, 130.65, 130.24, 129.96, 129.63,
129.44, 128.99, 128.28, 124.60, 119.12, 25.62, 21.82, 21.48,
20.80.LC/MZ(70 eV, APC1): 1044.70 [M+ + 2H+].
General procedure for the Suzuki–Miyaura
cross‑coupling reaction
Compounds (0.03 mmol), aryl chloride (1 mmol), phe-
nylboronic acid (1.5 mmol), base (2.0 mmol), and H2O/
DMF (2/2 mL) were added to a small Schlenk tube, and the
reaction mixture was heated up to various temperature for
diferent time. At the end of the reaction, the mixture was
cooled, extracted with ethyl acetate/hexane (1:5), and puri-
fed by fash chromatography on silica gel. The purity of
the compounds was checked by GC–MS. Conversions were
based on aryl chlorides.
Bis [(1-((2-hydroxynaphthalen-1-yl)methyleneamino)-
2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)(p-tolyl)
methanone] dichloro cobalt(II) (6) was prepared using
[(1-amino-2-thioxo-4-p-tolyl-1,2-dihydropyrimidin-5-yl)
(p-tolyl)methanone], 2-hydroxy-1-naphthaldehyde, and
cobalt(II) chloride. It was obtained as a dark-brown solid,
yield 51%; m.p. 199 °C (disintegration); UV (EtOH) λmax
(log ε) 320.2 (5.42) nm; FTIR γmax 1602, 1280, 751 cm−1.
1H NMR (DMSO-d6, 400 MHz,): δ: 11.99 (1 H, s), 11.80
Results and discussion
This report presented the synthesis, characterization, bio-
logic, catalytic, and spectral studies of the ligand (1) and
its fve new nickel, palladium, platinum, copper, and cobalt
1
complexes. According to FTIR, H NMR, and X-ray pow-
der difraction’s data, an octahedral geometry is observed
1 3